3-Chloro-4-fluorobenzaldehyde → HCID 66587060, compound

HRID 2047699Notes

Reaction equation

HRID 2047699 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH:14]=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH:14]=[N:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 5938663-Chloro-4-fluorobenzaldehydeHCID 38713955-Aminopyridine-2-carbonitrile

Product 1

HCID 66587060HCID 66587060, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 5-amino-2-cyanopyridine (2.86 g, 24 mmol), 3-chloro-4-fluoro-benzaldehyde (3.79 g, 24 mmol) and p-toluenesulfonic acid (92 mg, 0.5 mmol) in toluene (150 mL) was heated to reflux for 12 hours. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 5-[(3-chloro-4-fluoro-benzylidene)-amino]-pyridine-2-carbonitrile (5.8 g, 93.6%) as a light yellow solid. MS (ESI+) [(M+H)+] 260.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with ether

Sources & evidence

ORD record
ord-36b68f1d4f354ffa837fa3d66f30357d
Source dataset
uspto-grants-2013_11
Patent number
US08592594B2

Reaction notes

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